Salt of the optically-active laevo-o-dioxyphenylethanolmethylamin.



UNTTED @TATE% PATENT @FFTCE.

I FRANZ FLAECHER, OF HOGHST-ON-THE-MAIN, GERMANY, ASSIGNOR TO H. A. METZ&

(30., OF NEW YORK, N. Y., A CORPORATION OF NEW YORK.

SALT OF THE OPTICALLY-ACTIVE LAEVO-0-DIOXY1HENYLETHANOLMETHYLAMIN.

No Drawing.

Specification of Letters Patent.

Patented Mar. 7, 1911.

Application filed September 29, 1909. Serial No. 520,127. (Specimens)product itself. Such a salt has not hitherto been obtainable in spite ofthe numerous efforts made to produce it and it is of extreme importance,for so far as I am aware, it is.

only with its assistance that it becomes possible to prepare thel-o-dioxyphenylethanolmethylamin in such perfect purity as is requiredof a substance of such extraordinary pharmacological efficiency, and atthe same time one so readily oxidized. The treatment of the crude basegains in this way not only in simplicity, but in reliability as well,and the pure crystallized bi-tartrate of the optically activel-o-dioxyphenylethanolmethylamin represents a compound of ex-.

treine stability, the base linked to the acid being much lesssusceptible to oxidation than the free compound. I have found that awell crystallized salt of the l-odioxyphenylethanolmethylamin can beprepared by causing this base to react with tartaric acid,

excluding water as completely as possible. Whereas, for instance, it isnot possible to obtain crystals from a water solution ofl-o-dioxyphenylethanolmethylamin' in tartaric acid, even under extensiveevaporation of the solution the bi-tartrate is promptly crystallized inwell shaped crystals from a solution of one molecular equivalent of lodioxyphenylethanolmethylamin in one molecular equivalent of alcoholictartaric acid. Working witha methyl-alcoholic solution will be found tobe especially advantageous for the preparation of the salt. Forproducing this crystallized bi-tartrate of the optically active orthodioxyphenylethanolmethylamin, the optically inactivebase described inUnited States Patent Number 930,703 may be used as a parent product. Onemolecular equivalent of the latter is moistened with an equal quantityof absolute methyl-alcohol, and dissolved in a solution, heated to aboutfifty degrees, of one molecular equivalent of the commercialdextro-tartaric acid in three to four times its quantity ofmethyl-alcohol. When the mass becomes cold the bi -tartrate of thel-o-dioxyphenylethanolmethylamin isolates itself 1n coarse crystals,while the bi-tartrate of the dextro-ortho-dioxyphenylethanolmethylaminremains dissolved. The isolated salt is filtered off, washed withmethyl-alcohol and recrystallized from methyl-alcohol of ninety-five percent. strength, or from alco- 'hol of ninety per cent. strength, untilit shows the melting point of one hundred and forty-nine degrees C. v

The chemical reaction, .which preferably occurs at a temperature ofabout fifty degrees C. is as follows:

The lo dioxyphenylethanolmethylamin bi-tartrate melts at approximately149 degrees (3.; its water solution also rotates the ray of polarizedlight to the left amounting to about 13 degrees, [a]D:-l3 degrees. It

also possesses the hemostatio and bloodpressure raising prgperties ofthe su-prarenal gland. T

Some variations of the foregolng method may be found to be satisfactoryin the production of my product and I do not mean to limit myselfspecifically to the exact steps outlined, but

What I claim and desire to secure by Letters Patent is: r

1. The method of preparing a crystallized stable salt of the opticallyactive l-orthodioxyphenylethanolmethylamin,- consisting in causing onemolecular equivalent of the base to react with one molecular equivalentof tartaric acid excluding water as completely as possible.

2. The method of preparing a crystallized stable salt of the opticallyactive l-orthodioxyphenylethanolmethylamin, consisting in causing onemolecular equivalent of the base to react in an alcoholic solution withone molecular equivalent" of tartaric acid blood-pressure-raisingproperties of the su- 10 excluding water as completely as possible.prarenal gland.

3. As a new product, a stable crystallized In testimony whereof I havehereunto set acid salt of the. laevo-rotatory ortho-dioxy- In hand inthe presence of two subscribing phenylethanolmethylamin with tartaricwltnesses.

acid, consisting of a white crystalline pow- FRANZ FLAECHER. der whichis readily soluble in water, dif- Witnesses: ficultly soluble inalcohol, melting at 149 JEAN GRUND,

degrees C. and possessing the hemostatic and CARL GRUND.

